Branched fluorine-containing compound

ABSTRACT

A novel branched fluorine-containing compound represented by formula (1): 
       (Rf—Y n1 LX-A) n2   (1)
 
     wherein L represents a predetermined carbon-containing linker moiety; Rf, in each occurrence, is the same or different and represents fluoroalkyl optionally having at least one ether bond; Y, in each occurrence, is the same or different and represents a predetermined divalent linking group or a bond; R Y , in each occurrence, is the same or different and represents hydrogen or an organic group; L represents an (n1+n2)-valent carbon-containing linker moiety having at least one carbon atom; n1 represents a number greater than or equal to 1; n2 represents a number greater than or equal to 1; n1+n2 is a number from 3 to 6; X, in each occurrence, is the same or different and represents a divalent linking group or a bond; A, in each occurrence, is the same or different and represents —ArSO 3 M or the like; M, in each occurrence, is the same or different and represents hydrogen, —NR 4 , or a metal salt; and R represents hydrogen or a C 1-4  organic group.

TECHNICAL FIELD

The present invention relates to a branched fluorine-containingcompound.

BACKGROUND ART

Patent Literature 1 discloses, as a conventional branchedfluorine-containing compound, a branched fluorine-containing compounduseful as a surfactant.

CITATION LIST Patent Literature

PTL 1: WO2014/012661

SUMMARY OF INVENTION Technical Problem

However, there is a further need to develop a branchedfluorine-containing compound useful as a novel fluorine-containingsurfactant (in particular, an interface promoter, a viscosity reducer, adispersant, or an emulsifier).

Solution to Problem

The present inventors conducted extensive research, and found that theabove object can be achieved by a branched fluorine-containing compoundrepresented by formula (1):

(Rf—Y_(n1)LX-A)_(n2)  (1)

whereinL represents (1) a trivalent carbon-containing linker moiety representedby formula (L-1-1):

wherein R^(L), in each occurrence, is the same or different andrepresents hydrogen, alkyl, —NH₂, —NHR^(RL), —OH, or —OR^(RL), andR^(RL) represents an organic group,(2) a tetravalent carbon-containing linker moiety represented by formula(L-1-2):

wherein R^(L), in each occurrence, is the same or different andrepresents hydrogen, alkyl, —NH₂, —NHR^(RL), —OH, or —OR^(RL), andR^(RL) represents an organic group,(3) a pentavalent carbon-containing linker moiety represented by formula(L-1-3):

wherein R^(L) represents hydrogen, alkyl optionally having at least onesubstituent, —NH₂, —NHR^(RL), —OH, or —OR^(RL), and R^(RL) represents anorganic group,(4) a hexavalent carbon-containing linker moiety represented by formula(L-1-4):

(5) a tetravalent carbon-containing linker moiety represented by formula(L-2):

or(6) an (n1+n2)-valent carbon-containing linker moiety represented byformula (L-3):

wherein ring D represents an aromatic ring or a non-aromaticheterocycle;Rf, in each occurrence, is the same or different and representsfluoroalkyl optionally having at least one ether bond;Y, in each occurrence, is the same or different and represents (1) adivalent linking group selected from the group consisting of —O—, —COO—,—OCO—, —CONR^(Y)—, and —NR^(Y)CO— or (2) a bond, with the proviso thatwhen L is a trivalent carbon-containing linker moiety represented byformula (L-1-1) or a tetravalent carbon-containing linker moietyrepresented by formula (L-1-2), Y is not —COO— or —OCO—;R^(Y), in each occurrence, is the same or different and representshydrogen or an organic group;L represents an (n1+n2)-valent carbon-containing linker moiety having atleast one carbon atom;n1 represents a number greater than or equal to 1;n2 represents a number greater than or equal to 1;n1+n2 is a number from 3 to 6;X, in each occurrence, is the same or different and represents adivalent linking group or a bond;A, in each occurrence, is the same or different and represents —ArSO₃M,—SO₃M, —SO₄M, —PO₃M, or —COOM;M, in each occurrence, is the same or different and represents hydrogen,—NR₄, or a metal salt; andR, in each occurrence, is the same or different and represents hydrogenor a C₁₋₄ organic group.The present invention has thus been accomplished.

The present invention includes the following embodiments.

Item 1. A branched fluorine-containing compound represented by formula(1):

(Rf—Y_(n1)LX-A)_(n2)  (1)

whereinL represents (1) a trivalent carbon-containing linker moiety representedby formula (L-1-1):

wherein R^(L), in each occurrence, is the same or different andrepresents hydrogen, alkyl optionally having at least one substituent,—NH₂, —NHR^(RL), —OH, or —OR^(RL), and R^(RL) represents an organicgroup,(2) a tetravalent carbon-containing linker moiety represented by formula(L-1-2):

wherein R^(L), in each occurrence, is the same or different andrepresents hydrogen, alkyl optionally having at least one substituent,—NH₂, —NHR^(RL), —OH, or —OR^(RL), and R^(RL) represents an organicgroup,(3) a pentavalent carbon-containing linker moiety represented by formula(L-1-2):

wherein R^(L) represents hydrogen, alkyl optionally having at least onesubstituent, —NH₂, —NHR^(RL), —OH, or —OR^(RL), and R^(RL) represents anorganic group,(4) a hexavalent carbon-containing linker moiety represented by formula(L-1-2):

(5) a tetravalent carbon-containing linker moiety represented by formula(L-2):

or(6) an (n1+n2)-valent carbon-containing linker moiety represented byformula (L-3):

wherein ring D represents an aromatic ring or a non-aromaticheterocycle;Rf, in each occurrence, is the same or different and representsfluoroalkyl optionally having at least one ether bond;Y, in each occurrence, is the same or different and represents (1) adivalent linking group selected from the group consisting of —O—, —COO—,—OCO—, —CONR^(Y)—, and —NR^(Y)CO— or (2) a bond, with the proviso thatwhen L is a trivalent carbon-containing linker moiety represented byformula (L-1-1) or a tetravalent carbon-containing linker moietyrepresented by formula (L-1-2), Y is not —COO— or —OCO—;R^(Y), in each occurrence, is the same or different and representshydrogen or an organic group;L represents an (n1+n2)-valent carbon-containing linker moiety having atleast one carbon atom;n1 represents a number greater than or equal to 1;n2 represents a number greater than or equal to 1;n1+n2 is a number from 3 to 6;X, in each occurrence, is the same or different and represents adivalent linking group or a bond;A, in each occurrence, is the same or different and represents —ArSO₃M,—SO₃M, —SO₄M, —PO₃M, or —COOM;M, in each occurrence, is the same or different and represents hydrogen,—NR₄, or a metal salt; andR represents hydrogen or a C₁₋₄ organic group.Item 2. The branched fluorine-containing compound according to Item 1,wherein L is a trivalent carbon-containing linker moiety represented byformula (L-1-1) or a tetravalent carbon-containing linker moietyrepresented by formula (L-1-2); and Y, in each occurrence, is the sameor different and represents (1) a divalent linking group selected fromthe group consisting of —O—, —CONR^(Y)—, and —NR^(Y)CO— or (2) a bond.Item 3. The branched fluorine-containing compound according to Item 2,wherein X is an alkylene chain or a bond.Item 4. The branched fluorine-containing compound according to Item 3,wherein X is a bond.Item 5. The branched fluorine-containing compound according to Item 1,wherein L is a tetravalent carbon-containing linker moiety representedby formula (L-2); and at least one Y is —O—, —COO—, —OCO—, —CONR^(Y)—,or —NR^(Y)CO—.Item 6. The branched fluorine-containing compound according to any oneof Items 1 to 4, wherein n1 is 1 or 2; and n2 is 2.

The present invention further includes the following embodiments.

Item 7. A surfactant comprising the branched fluorine-containingcompound according to any one of Items 1 to 6.Item 8. An aqueous dispersant comprising the branchedfluorine-containing compound according to any one of Items 1 to 6.

Advantageous Effects of Invention

The present invention provides a novel branched fluorine-containingcompound.

In an embodiment of the present invention, the branchedfluorine-containing compound is useful as an emulsifier.

DESCRIPTION OF EMBODIMENTS Terms

The symbols and the abbreviations in this specification are to beinterpreted as having the general meanings in the related technicalfield to which the present invention pertains, according to the contextof this specification, unless otherwise specified.

In this specification, the term “comprise” or “contain” is intended toencompass the meanings of “consist essentially of” and “consist of.”

The steps, treatments, or operations in this specification can beperformed at room temperature, unless otherwise specified.

In this specification, room temperature refers to a temperature in therange of 10 to 40° C.

In this specification, the term “Cn-m” (herein, n and m are numbers)indicates that the carbon number is n or more and m or less, as usuallyunderstood by a person skilled in the art.

In this specification, unless otherwise specified, examples of “halogenatom” include fluorine, chlorine, bromine, and iodine.

In this specification, the term “organic group” refers to a groupcontaining at least one carbon atom, or a group formed by removing onehydrogen atom from an organic compound.

Examples of “organic group” include the following:

alkyl optionally having at least one substituent,alkenyl optionally having at least one substituent,alkynyl optionally having at least one substituent,cycloalkyl optionally having at least one substituent,cycloalkenyl optionally having at least one substituent,cycloalkadienyl optionally having at least one substituent,aryl optionally having at least one substituent,aralkyl optionally having at least one substituent,non-aromatic heterocyclic group optionally having at least onesubstituent,heteroaryl optionally having at least one substituent,cyano,aldehyde,

R^(a)O—, R^(a)CO—,

R^(a)SO₂—,

R^(a)OCO—, and

R^(a)OSO₂—wherein R^(a) is independentlyalkyl optionally having at least one substituent,alkenyl optionally having at least one substituent,alkynyl optionally having at least one substituent,cycloalkyl optionally having at least one substituent,cycloalkenyl optionally having at least one substituent,cycloalkadienyl optionally having at least one substituent,aryl optionally having at least one substituent,aralkyl optionally having at least one substituent,non-aromatic heterocyclic group optionally having at least onesubstituent, orheteroaryl optionally having at least one substituent.

In this specification, examples of the substituent in each of alkyloptionally having at least one substituent, alkenyl optionally having atleast one substituent, alkynyl optionally having at least onesubstituent, cycloalkyl optionally having at least one substituent,cycloalkenyl optionally having at least one substituent, cycloalkadienyloptionally having at least one substituent, aryl optionally having atleast one substituent, aralkyl optionally having at least onesubstituent, non-aromatic heterocyclic group optionally having at leastone substituent, and heteroaryl optionally having at least onesubstituent include nitro, hydroxy, halogen, cyano, aliphatic group,aryl, heterocyclyl, acyl, acyloxy, acylamino, aliphatic oxy, aryloxy,heterocyclyloxy, aliphatic oxycarbonyl, aryloxycarbonyl,heterocyclyloxycarbonyl, carbamoyl, aliphatic sulfonyl, arylsulfonyl,heterocyclylsulfonyl, aliphatic sulfonyloxy, arylsulfonyloxy,heterocyclylsulfonyloxy, sulfamoyl, aliphatic sulfonamide,arylsulfonamide, heterocyclylsulfonamide, amino, aliphatic amino,arylamino, heterocyclylamino, aliphatic oxycarbonylamino,aryloxycarbonylamino, heterocyclyloxycarbonylamino, aliphatic sulfinyl,arylsulfinyl, aliphatic thio, arylthio, sulfo, carboxy, aliphaticoxyamino, aryloxyamino, carbamoylamino, sulfamoylamino, halogen,sulfamoylcarbamoyl, carbamoylsulfamoyl, dialiphatic oxyphosphinyl, anddiaryloxyphosphinyl (the group consisting of these substituents may bereferred to as “substituent group A”); and preferably include

(a) halogen,(b) hydroxy,(c) nitro, and(d) cyano.

The term “aryl” in the substituent group A can mean an aryl group or anaryl moiety.

The term “aliphatic” in the substituent group A can mean an aliphaticgroup or an aliphatic moiety.

In substituents or part thereof of the substituent group A, the term“aliphatic (group or moiety)” may have at least one substituent, and maybe saturated or unsaturated.

The substituent may be any group with which the “aliphatic (group ormoiety)” can be substituted, among the substituent group A.

Examples of the substituent include hydroxy, aliphatic oxy, carbamoyl,aliphatic oxycarbonyl, aliphatic thio, amino, aliphatic amino,acylamino, and carbamoylamino.

The term “aliphatic (group or moiety)” is preferably C₁₋₈ alkyl, andmore preferably C₁₋₄ alkyl. Examples of “aliphatic (group or moiety)”include methyl, ethyl, vinyl, cyclohexyl, and carbamoylmethyl.

In substituents or part thereof of the substituent group A, the “aryl(group or moiety)” may be fused with at least one ring (e.g., a 3- to8-membered non-aromatic heterocycle, a 5- or 6-membered aromaticheterocycle, a C₃₋₈ non-aromatic carbocycle), and may have asubstituent(s).

The substituent may be any group with which the “aryl (group or moiety)”can be substituted, among the substituent group A.

Examples of the substituent include nitro, halogen, aliphatic oxy,carbamoyl, aliphatic oxycarbonyl, aliphatic thio, amino, aliphaticamino, acylamino, and carbamoylamino.

The term “aryl (group or moiety)” is preferably C₆₋₁₂ aryl, and morepreferably C₆₋₁₀ aryl.

Examples of “aryl (group or moiety)” include phenyl, 4-nitrophenyl,4-acetylaminophenyl, and 4-methanesulfonylphenyl.

In substituents or part thereof of the substituent group A, the term“heterocyclyl (group or moiety)” may have a substituent(s), may besaturated or unsaturated, and may be fused with a ring(s). Specifically,the term “heterocyclyl (group or moiety)” may be the aforementionednon-aromatic heterocyclic group or heteroaryl.

The substituent may be any group with which the “heterocyclyl (group ormoiety)” can be substituted, among the substituent group A.

Examples of the substituent include halogen, hydroxy, aliphatic oxy,carbamoyl, aliphatic oxycarbonyl, aliphatic thio, amino, aliphaticamino, acylamino, and carbamoylamino.

In substituents or part thereof of the substituent group A, the term“heterocyclyl (group or moiety)” is preferably C₂₋₁₂ 5- to 14-memberedheterocyclyl that is bonded via a carbon atom thereof, and morepreferably C₂₋₁₀ 5- to 14-membered heterocyclyl that is bonded via acarbon atom thereof.

Examples of “heterocyclyl (group or moiety)” include 2-tetrahydrofuryland 2-pyrimidyl.

In substituents or part thereof of the substituent group A, the term“acyl (group or moiety)” may be aliphatic carbonyl, arylcarbonyl, orheterocyclylcarbonyl, and may have a substituent(s).

The substituent may be any group with which the “acyl (group or moiety)”can be substituted, among the substituent group A.

Examples of the substituent include hydroxy, halogen, aryl, aliphaticoxy, carbamoyl, aliphatic oxycarbonyl, aliphatic thio, amino, aliphaticamino, acylamino, and carbamoylamino.

The term “acyl (group or moiety)” is preferably C₂₋₈ acyl, and morepreferably C₂₋₄ acyl.

Examples of “acyl (group or moiety)” include acetyl, propanoyl, benzoyl,and 3-pyridinecarbonyl.

In substituents or part thereof of the substituent group A, the term“carbamoyl (group or moiety)” may have a substituent(s).

The substituent may be any group with which the “carbamoyl (group ormoiety)” can be substituted, among the substituent group A.

Examples of the substituent include an aliphatic group, aryl, andheterocyclyl.

The term “carbamoyl” is preferably unsubstituted carbamoyl oralkylcarbamoyl having a total of 2 to 9 (preferably 2 to 5) carbonatoms.

Examples of “carbamoyl” include N-methylcarbamoyl,N,N-dimethylcarbamoyl, and N-phenylcarbamoyl.

In this specification, examples of the substituent in each of cycloalkyloptionally having at least one substituent, cycloalkenyl optionallyhaving at least one substituent, cycloalkadienyl optionally having atleast one substituent, aryl optionally having at least one substituent,aralkyl optionally having at least one substituent, non-aromaticheterocyclic group optionally having at least one substituent, andheteroaryl optionally having at least one substituent further include(e) alkyl optionally having at least one substituent, (f) alkenyloptionally having at least one substituent, and (g) alkynyl optionallyhaving at least one substituent.

In this specification, unless otherwise specified, the term “alkyl” maybe linear or branched.

In this specification, unless otherwise specified, preferable examplesof “alkyl” include C₁₋₂₀ alkyl, C₁₋₈ alkyl, C₁₋₇ alkyl, C₁₋₆ alkyl, andC₁₋₅ alkyl.

In this specification, unless otherwise specified, specific examples of“alkyl” include methyl, ethyl, propyl, isopropyl, butyl, isobutyl,sec-butyl, tert-butyl, pentyl, isopentyl, neopentyl, hexyl, heptyl,octyl, nonyl, and decyl.

In this specification, specific examples of “C₁₋₈ alkyl” include alkylhaving 1 to 8 carbon atoms among the aforementioned specific examples ofalkyl, as naturally understood by a person skilled in the art. As aprecaution, specific examples of “C₁₋₈ alkyl” include linear or branchedC₁₋₈ alkyl.

In this specification, the term “fluoroalkyl optionally having at leastone ether bond” may be fluoroalkyl into which at least one ethericoxygen atom may be inserted.

Examples thereof include

(1) alkyl substituted with at least one fluorine atom; and(2) alkyl having at least one ether bond and substituted with at leastone fluorine atom.

In this specification, the term “fluoroalkyl” encompassesperfluoroalkyl.

In this specification, specific examples of “fluoroalkyl” include CF₃—,C₂F₅—, C₃F₇—, C₂F₅CH₂—, H(CF₂CF₂)₂CH₂—, and H(CF₂CF₂)₃CH₂—.

In this specification, specific examples of fluoroalkyl having at leastone ether bond include CF₃OC₂F₄—, CF₃OC₃F₆—, CF₃OC₄F₈—, CF₃OC₅F₁₀—,CF₃OC₂F₄OC₂F₄—, C₂F₅OC₂F₄—, C₂F₅OC₃F₆—, C₂F₅OC₄F₈—, C₂F₅OC₂F₄OC₂F₄—,C₃F₇O(CF₂)₂—, C₃F₇OCF(CF₃)—, C₃F₇OC₃F₆—, and C₄F₉OC₂F₄—.

In this specification, unless otherwise specified, examples of “alkenyl”include linear or branched C₂₋₁₀ alkenyl, such as vinyl, 1-propen-1-yl,2-propen-1-yl, isopropenyl, 2-buten-1-yl, 4-penten-1-yl, and5-hexen-1-yl.

In this specification, unless otherwise specified, examples of “alkynyl”include linear or branched C₂₋₁₀ alkynyl, such as ethynyl,1-propyn-1-yl, 2-propyn-1-yl, 4-pentyn-1-yl, and 5-hexyne-1-yl.

In this specification, unless otherwise specified, examples of“cycloalkyl” include C₃₋₁₀ cycloalkyl, such as cyclopropyl, cyclobutyl,cyclopentyl, cyclohexyl, and cycloheptyl.

In this specification, unless otherwise specified, examples of“cycloalkenyl” include C₃₋₁₀ cycloalkenyl, such as cyclopropenyl,cyclobutenyl, cyclopentenyl, cyclohexenyl, and cycloheptenyl.

In this specification, unless otherwise specified, examples of“cycloalkadienyl” include C₄₋₁₀ cycloalkadienyl, such ascyclobutadienyl, cyclopentadienyl, cyclohexadienyl, cycloheptadienyl,cyclooctadienyl, cyclononadienyl, and cyclodecadienyl.

In this specification, unless otherwise specified, the term “aryl” maybe monocyclic, bicyclic, tricyclic, or tetracyclic.

In this specification, unless otherwise specified, the term “aryl” maybe C₆₋₁₈ aryl.

In this specification, unless otherwise specified, examples of “aryl”include phenyl, 1-naphthyl, 2-naphthyl, 2-biphenyl, 3-biphenyl,4-biphenyl, and 2-anthryl.

In this specification, unless otherwise specified, examples of “aralkyl”include benzyl, phenethyl, diphenylmethyl, 1-naphthyl methyl, 2-naphthylmethyl, 2,2-diphenylethyl, 3-phenylpropyl, 4-phenylbutyl,5-phenylpentyl, 2-biphenylylmethyl, 3-biphenylylmethyl, and4-biphenylylmethyl.

In this specification, unless otherwise specified, the term“non-aromatic heterocyclic group” may be monocyclic, bicyclic,tricyclic, or tetracyclic.

In this specification, unless otherwise specified, the term“non-aromatic heterocyclic group” may be, for example, a non-aromaticheterocyclic group containing, in addition to carbon, 1 to 4 heteroatomsselected from oxygen, sulfur, and nitrogen as a ring-constituting atom.

In this specification, unless otherwise specified, the term“non-aromatic heterocyclic group” may be saturated or unsaturated.

In this specification, unless otherwise specified, examples of“non-aromatic heterocyclic group” include tetrahydrofuryl, oxazolidinyl,imidazolinyl (e.g., 1-imidazolinyl, 2-imidazolinyl, and 4-imidazolinyl),aziridinyl (e.g., 1-aziridinyl and 2-aziridinyl), azetidinyl (e.g.,1-azetidinyl and 2-azetidinyl), pyrrolidinyl (e.g., 1-pyrrolidinyl,2-pyrrolidinyl, and 3-pyrrolidinyl), piperidinyl (e.g., 1-piperidinyl,2-piperidinyl, and 3-piperidinyl), azepanyl (e.g., 1-azepanyl,2-azepanyl, 3-azepanyl, and 4-azepanyl), azocanyl (e.g., 1-azocanyl,2-azocanyl, 3-azocanyl, and 4-azocanyl), piperazinyl (e.g.,1,4-piperazin-1-yl and 1,4-piperazin-2-yl), diazepinyl (e.g.,1,4-diazepin-1-yl, 1,4-diazepin-2-yl, 1,4-diazepin-5-yl, and1,4-diazepin-6-yl), diazocanyl (e.g., 1,4-diazocan-1-yl,1,4-diazocan-2-yl, 1,4-diazocan-5-yl, 1,4-diazocan-6-yl,1,5-diazocan-1-yl, 1,5-diazocan-2-yl, and 1,5-diazocan-3-yl),tetrahydropyranyl (e.g., tetrahydropyran-4-yl), morpholinyl (e.g.,4-morpholinyl), thiomorpholinyl (e.g., 4-thiomorpholinyl),2-oxazolidinyl, dihydrofuryl, dihydropyranyl, dihydroquinolyl, and thelike.

In this specification, unless otherwise specified, the term “heteroaryl”may be, for example, a monocyclic, bicyclic, tricyclic, or tetracyclic,5- to 18-membered heteroaryl.

In this specification, unless otherwise specified, the term “heteroaryl”is, for example, heteroaryl containing, in addition to carbon, 1 to 4heteroatoms selected from oxygen, sulfur, and nitrogen as aring-constituting atom. The term “heteroaryl” may have, for example, 3to 17 carbon atoms.

In this specification, unless otherwise specified, the term “heteroaryl”encompasses monocyclic heteroaryl and aromatic fused heterocyclic group.

In this specification, unless otherwise specified, examples of“monocyclic heteroaryl” include pyrrolyl (e.g., 1-pyrrolyl, 2-pyrrolyl,and 3-pyrrolyl), furyl (e.g., 2-furyl and 3-furyl), thienyl (e.g.,2-thienyl and 3-thienyl), pyrazolyl (e.g., 1-pyrazolyl, 3-pyrazolyl, and4-pyrazolyl), imidazolyl (e.g., 1-imidazolyl, 2-imidazolyl, and4-imidazolyl), isoxazolyl (e.g., 3-isoxazolyl, 4-isoxazolyl, and5-isoxazolyl), oxazolyl (e.g., 2-oxazolyl, 4-oxazolyl, and 5-oxazolyl),isothiazolyl (e.g., 3-isothiazolyl, 4-isothiazolyl, and 5-isothiazolyl),thiazolyl (e.g., 2-thiazolyl, 4-thiazolyl, and 5-thiazolyl), triazolyl(e.g., 1,2,3-triazol-4-yl and 1,2,4-triazol-3-yl), oxadiazolyl (e.g.,1,2,4-oxadiazol-3-yl and 1,2,4-oxadiazol-5-yl), thiadiazolyl (e.g.,1,2,4-thiadiazol-3-yl and 1,2,4-thiadiazol-5-yl), tetrazolyl, pyridyl(e.g., 2-pyridyl, 3-pyridyl, and 4-pyridyl), pyridazinyl (e.g.,3-pyridazinyl and 4-pyridazinyl), pyrimidinyl (e.g., 2-pyrimidinyl,4-pyrimidinyl, and 5-pyrimidinyl), pyrazinyl, and the like.

In this specification, unless otherwise specified, examples of “aromaticfused heterocyclic group” include isoindolyl (e.g., 1-isoindolyl,2-isoindolyl, 3-isoindolyl, 4-isoindolyl, 5-isoindolyl, 6-isoindolyl,and 7-isoindolyl), indolyl (e.g., 1-indolyl, 2-indolyl, 3-indolyl,4-indolyl, 5-indolyl, 6-indolyl, and 7-indolyl), benzo[b]furanyl (e.g.,2-benzo[b]furanyl, 3-benzo[b]furanyl, 4-benzo[b]furanyl,5-benzo[b]furanyl, 6-benzo[b]furanyl, and 7-benzo[b]furanyl),benzo[c]furanyl (e.g., 1-benzo[c]furanyl, 4-benzo[c]furanyl, and5-benzo[c]furanyl), benzo[b]thienyl (e.g., 2-benzo[b]thienyl,3-benzo[b]thienyl, 4-benzo[b]thienyl, 5-benzo[b]thienyl,6-benzo[b]thienyl, and 7-benzo[b]thienyl), benzo[c]thienyl (e.g.,1-benzo[c]thienyl, 4-benzo[c]thienyl, and 5-benzo[c]thienyl), indazolyl(e.g., 1-indazolyl, 2-indazolyl, 3-indazolyl, 4-indazolyl, 5-indazolyl,6-indazolyl, and 7-indazolyl), benzimidazolyl (e.g., 1-benzimidazolyl,2-benzimidazolyl, 4-benzimidazolyl, and 5-benzimidazolyl),1,2-benzisoxazolyl (e.g., 1,2-benzisoxazol-3-yl, 1,2-benzisoxazol-4-yl,1,2-benzisoxazol-5-yl, 1,2-benzisoxazol-6-yl, and1,2-benzisoxazol-7-yl), benzoxazolyl (e.g., 2-benzoxazolyl,4-benzoxazolyl, 5-benzoxazolyl, 6-benzoxazolyl, and 7-benzoxazolyl),1,2-benzisothiazolyl (e.g., 1,2-benzisothiazol-3-yl,1,2-benzisothiazol-4-yl, 1,2-benzisothiazol-5-yl,1,2-benzisothiazol-6-yl, and 1,2-benzisothiazol-7-yl), benzothiazolyl(e.g., 2-benzothiazolyl, 4-benzothiazolyl, 5-benzothiazolyl,6-benzothiazolyl, and 7-benzothiazolyl), isoquinolyl (e.g.,1-isoquinolyl, 3-isoquinolyl, 4-isoquinolyl, and 5-isoquinolyl),quinolyl (e.g., 2-quinolyl, 3-quinolyl, 4-quinolyl, 5-quinolyl, and8-quinolyl), cinnolinyl (e.g., 3-cinnolinyl, 4-cinnolinyl, 5-cinnolinyl,6-cinnolinyl, 7-cinnolinyl, and 8-cinnolinyl), phthalazinyl (e.g.,1-phthalazinyl, 4-phthalazinyl, 5-phthalazinyl, 6-phthalazinyl,7-phthalazinyl, and 8-phthalazinyl), quinazolinyl (e.g., 2-quinazolinyl,4-quinazolinyl, 5-quinazolinyl, 6-quinazolinyl, 7-quinazolinyl, and8-quinazolinyl), quinoxalinyl (e.g., 2-quinoxalinyl, 3-quinoxalinyl,5-quinoxalinyl, 6-quinoxalinyl, 7-quinoxalinyl, and 8-quinoxalinyl),pyrazolo[1,5-a]pyridyl (e.g., pyrazolo[1,5-a]pyridin-2-yl,pyrazolo[1,5-a]pyridin-3-yl, pyrazolo[1,5-a]pyridin-4-yl,pyrazolo[1,5-a]pyridin-5-yl, pyrazolo[1,5-a]pyridin-6-yl, andpyrazolo[1,5-a]pyridin-7-yl), imidazo[1,2-a]pyridyl (e.g.,imidazo[1,2-a]pyridin-2-yl, imidazo[1,2-a]pyridin-3-yl,imidazo[1,2-a]pyridin-5-yl, imidazo[1,2-a]pyridin-6-yl,imidazo[1,2-a]pyridin-7-yl, and imidazo[1,2-a]pyridin-8-yl), and thelike.

In this specification, unless otherwise specified, examples of aromaticrings include aromatic carbocycles and aromatic heterocycles.

In this specification, unless otherwise specified, examples of aromaticcarbocycles include a benzene ring, a naphthalene ring, and ananthracene ring.

In this specification, unless otherwise specified, examples of aromaticheterocycles include

(1) 5- or 6-membered aromatic heterocycles; specific examples thereofinclude a furan ring, a thiophene ring, a pyrrole ring, an oxazole ring,an isoxazole ring, a thiazole ring, an isothiazole ring, an imidazolering, a pyrazole ring, a 1,2,3-oxadiazole ring, a 1,2,4-oxadiazole ring,a 1,3,4-oxadiazole ring, a furazan ring, a 1,2,3-thiadiazole ring, a1,2,4-thiadiazole ring, a 1,3,4-thiadiazole ring, a 1,2,3-triazole ring,a 1,2,4-triazole ring, a tetrazole ring, a pyridine ring, a pyridazinering, a pyrimidine ring, a pyrazine ring, a triazine ring, and the like;(2) rings formed by fusing two of the aforementioned 5- or 6-memberedaromatic heterocycles; and(3) rings formed by fusing one of the aforementioned 5- or 6-memberedaromatic heterocycles and a benzene ring.

In this specification, unless otherwise specified, examples ofnon-aromatic heterocycles include 3- to 8-membered non-aromaticheterocycles containing, in addition to carbon, 1 to 4 heteroatomsselected from oxygen, sulfur, and nitrogen as a ring-constituting atom,and the like. Specific examples thereof include oxirane, azetidine,oxetane, thietane, pyrrolidine, dihydrofuran, tetrahydrofuran,tetrahydrothiophene, imidazolidine, oxazolidine, isoxazoline,piperidine, dihydropyran, tetrahydropyran, tetrahydrothiopyran,morpholine, thiomorpholine, piperazine, dihydrooxazine,tetrahydrooxazine, dihydropyrimidine, tetrahydropyrimidine, azepane,oxepane, thiepane, oxazepane, thiazepane, azocane, oxocane, thiocane,oxazocane, thiazocane, and the like.

In this specification, examples of “alkali metal” include lithium,sodium, potassium, rubidium, and cesium.

In this specification, the term “alkylene chain” may be a divalent groupformed by removing one hydrogen atom from the alkyl described above.

Compound

The compound of the present invention is a branched fluorine-containingcompound represented by formula (1) (which may be referred to as“compound (1)” in this specification).

The symbols in formula (1) are explained below.

L represents (1) a trivalent carbon-containing linker moiety representedby formula (L-1-1):

wherein R^(L), in each occurrence, is the same or different andrepresents hydrogen, alkyl optionally having at least one substituent,—NH₂, —NHR^(RL), —OH, or —OR^(RL), and R^(RL) represents an organicgroup,(2) a tetravalent carbon-containing linker moiety represented by formula(L-1-2):

wherein R^(L), in each occurrence, is the same or different andrepresents hydrogen, alkyl optionally having at least one substituent,—NH₂, —NHR^(RL), —OH, or —OR^(RL), and R^(RL) represents a substituent,(3) a pentavalent carbon-containing linker moiety represented by formula(L-1-3):

wherein R^(L) represents hydrogen, alkyl optionally having at least onesubstituent, —NH₂, —NHR^(RL), —OH, or —OR^(RL), and R^(RL) represents anorganic group,(4) a hexavalent carbon-containing linker moiety represented by formula(L-1-4):

(5) a tetravalent carbon-containing linker moiety represented by formula(L-2):

or(6) an (n1+n2)-valent carbon-containing aromatic linker moietyrepresented by formula (L-3):

wherein ring D represents an aromatic ring.

In each of these partial structural formulas, the alkyl of “alkyloptionally having at least one substituent” represented by R^(L) is thesame or different and is preferably C₁₋₁₀ alkyl.

Among the carbon-containing linker moieties represented by formulas(L-1-1), (L-1-2), (L-1-3), and (L-1-4), a trivalent carbon-containinglinker moiety represented by formula (L-1-1) or a tetravalentcarbon-containing linker moiety represented by formula (L-1-2) ispreferable.

n1 is a number greater than or equal to 1 (preferably a number from 1 to5).

n1 may be, for example, 1, 2, 3, or 4 (preferably 1 or 2, and morepreferably 2).

n2 is a number greater than or equal to 1 (preferably a number from 1 to5).

n2 may be, for example, 1, 2, 3, or 4 (preferably 1 or 2, and morepreferably 2).

n1+n2 may be, for example, 3, 4, 5, or 6 (preferably 3 or 4).

In another preferred embodiment of the present invention,

L is a linker moiety represented by formula (L-1-1), (L-1-2), (L-2), or(L-3);n1 is 1 or 2; andn2 is 2.

In another preferred embodiment of the present invention,

L is a linker moiety represented by formula (L-1-2), (L-2), or (L-3)(preferably formula (L-1-2));n1+n2 is 4; and(a) n1 is 3, and n2 is 1, or(b) n1 is 1, and n2 is 3.

In another preferred embodiment of the present invention,

L is a linker moiety represented by formula (L-1-3) or (L-3) (preferablyformula (L-1-3));n1+n2 is 5; and(a) n1 is 4, and n2 is 1,(b) n1 is 3, and n2 is 2,(c) n1 is 2, and n2 is 3, or(d) n1 is 1, and n2 is 4.

In another preferred embodiment of the present invention,

L is a linker moiety represented by formula (L-1-4) or (L-3) (preferablyformula (L-1-4));n1+n2 is 6; and(a) n1 is 5, and n2 is 1,(b) n1 is 4, and n2 is 2,(c) n1 is 3, and n2 is 3,(d) n1 is 2, and n2 is 4, or(e) n1 is 1, and n2 is 5.

In another preferred embodiment of the present invention,

L is a linker moiety represented by formula (L-1-2), (L-2), or (L-3);n1 is 3; andn2 is 1.

The direction of the partial structural formula of formula (L-1-1),(L-1-2), (L-2), or (L-3), and the direction of the structural formula offormula (1) may be the same or different.

Thus, as easily understood by a person skilled in the art, the asterisks(*) in formula (L-1-1), (L-1-2), (L-2), or (L-3) each independentlyrepresent a bonding site to Rf—Y— or —X-A.

In a preferred embodiment of compound (1) having a carbon-containinglinker moiety represented by formula (L-1-1), compound (1) has two Rf—Y—groups, and has a structure represented by the following formula(1-L-1-1A):

wherein the symbols in the formula are as defined above.

In a preferred embodiment of compound (1) having a carbon-containinglinker moiety represented by formula (L-1-1), compound (1) has two —X-Agroups, and has a structure represented by the following formula(1-L-1-1B):

wherein the symbols in the formula are as defined above.

In a preferred embodiment of compound (1) having a carbon-containinglinker moiety represented by formula (L-1-2), compound (1) has two Rf—Y—groups and two —X-A groups, and has a structure represented by thefollowing formula (1-L-1-2):

wherein the symbols in the formula are as defined above.

In a preferred embodiment of compound (1) having a carbon-containinglinker moiety represented by formula (L-2), compound (1) has two Rf—Y—groups and two —X-A groups, and a carbon-containing linker moietyderived from a benzene ring, and has a structure represented by thefollowing formula (1-2):

wherein the symbols in the formula are as defined above.

Rf, in each occurrence, is the same or different and representsfluoroalkyl optionally having at least one ether bond.

Rf, in each occurrence, is the same or different and is preferably C₁₋₂₀fluoroalkyl optionally having at least one ether bond, more preferablyC₁₋₈ fluoroalkyl optionally having at least one ether bond, even morepreferably C₁₋₇ fluoroalkyl optionally having at least one ether bond,still even more preferably C₁₋₆ fluoroalkyl optionally having at leastone ether bond, and particularly preferably C₁₋₅ fluoroalkyl optionallyhaving at least one ether bond.

Rf is preferably fluoroalkyl containing a C₁₋₅ perfluoroalkyl moiety(which may have at least one ether bond).

Y, in each occurrence, is the same or different and represents (1) adivalent linking group selected from the group consisting of —O—, —COO—,—OCO—, —CONR^(Y)—, and —NR^(Y)CO— or (2) a bond, with the proviso thatwhen L is a linker moiety represented by formula (L-1-1) or (L-1-2), Yis not —COO— or —OCO—.

In a preferred embodiment of the present invention, L is a trivalentcarbon-containing linker moiety represented by formula (L-1-1) or atetravalent carbon-containing linker moiety represented by formula(L-1-2); and

preferably, Y, in each occurrence, is the same or different (preferably,in each occurrence, is the same) and represents (1) a divalent linkinggroup selected from the group consisting of —O—, —CONR^(Y)—, and—NR^(Y)CO— or (2) a bond.

The compound of this embodiment is particularly excellent in stability(in particular, under acidic or basic conditions).

R^(Y), in each occurrence, is the same or different (preferably, in eachoccurrence, is the same) and represents hydrogen or an organic group.

Preferably, R^(Y), in each occurrence, is the same or different(preferably, in each occurrence, is the same) and represents methyl,trifluoromethyl or hydrogen.

R^(Y) is more preferably hydrogen.

More preferably, Y, in each occurrence, is the same or different(preferably, in each occurrence, is the same) and represents —CONH—,—NHCO—, or —O—.

X, in each occurrence, is the same or different and represents adivalent linking group or a bond.

Preferably, X, in each occurrence, is the same or different (preferably,in each occurrence, is the same) and represents an alkylene chain or abond.

X is more preferably a bond.

In a preferred embodiment of the present invention, L is a tetravalentcarbon-containing linker moiety represented by formula (L-2); and atleast one Y is —O—, —COO—, —OCO—, —CONR^(Y)—, or —NR^(Y)CO—.

In a preferred embodiment of the present invention, n1 is 1 or 2; and n2is 2.

A, in each occurrence, is the same or different (preferably, in eachoccurrence, is the same) and represents —ArSO₃M, —SO₃M, —SO₄M, —PO₃M, or—COOM.

A is preferably —COOM or —SO₃M, and more preferably —COOM.

M, in each occurrence, is the same or different (preferably, in eachoccurrence, is the same) and represents hydrogen, —NR₄, or a metal salt.

R, in each occurrence, is the same or different and represents hydrogenor a C₁₋₄ organic group.

M is preferably —NH₄.

The compound of a particularly preferred embodiment of the presentinvention is a branched fluorine-containing compound represented by thefollowing:

whereinRf, in each occurrence, is the same or different and representsfluoroalkyl optionally having at least one ether bond;Y, in each occurrence, is the same or different and represents (1) adivalent linking group selected from the group consisting of —O—,—CONH—, and —NHCO— or (2) a bond;X represents a bond; andA represents —COONH₄.

The compound of another particularly preferred embodiment of the presentinvention is a branched fluorine-containing compound represented by thefollowing:

whereinRf, in each occurrence, is the same or different and representsfluoroalkyl optionally having at least one ether bond;Y, in each occurrence, is the same or different and represents (1) adivalent linking group selected from the group consisting of —O—,—CONH—, and —NHCO— or (2) a bond; X represents a bond; andA represents —COONH₄.

The compound of still another particularly preferred embodiment of thepresent invention is a branched fluorine-containing compound representedby the following:

whereinRf, in each occurrence, is the same or different and representsfluoroalkyl optionally having at least one ether bond;Y, in each occurrence, is the same or different and represents (1) adivalent linking group selected from the group consisting of —O—,—CONH—, and —NHCO— or (2) a bond;X represents a bond; andA represents —COONH₄.

Synthesis Method for Compound

The compound of the present invention can be synthesized by a knownmethod, a method similar to a known method, or a combination thereof.

Specifically, for example, compound (1) of the present invention inwhich A is —COONH₄ can be synthesized by, for instance, adding anammonia methanol solution to a compound of formula (1) in which A is—COOH. The compound of formula (1) in which A is —COOH can be producedaccording to a known method, or is commercially available.

Specifically, for example, compound (1) having a carbon-containinglinker moiety represented by formula (L-1-1), (L-1-2), (L-2), or (L-3)can be synthesized by causing a base to act on a carboxylic acid havingthe carbon-containing linker moiety or an ester thereof (e.g.,dihydroxysuccinic acid (tartaric acid), methyl dihydroxysuccinate,monoaminosuccinic acid (aspartic acid), diaminosuccinic acid, or diethylmalonate) as necessary, and then adding a fluorine-containing compound(e.g., CF₃COOCOCF₃, CF₃COOCH₃, C₃F₇₀OCF(CF₃) COOCH₃, CF₂═CFOCF₂CF₂CF₃,and CF₃CF₂CF₂CF₂CH₂CH₂I) as an electrophile. Such a carboxylic acid oran ester thereof can be produced according to a known method, or iscommercially available.

The compound of the present invention can suitably decrease the surfacetension of water.

The compound of the present invention can be suitably used as asurfactant.

The compound of the present invention can be suitably used as aninterface promoter (in particular, an interface promoter in, forexample, coating materials, lacquers, or adhesives).

The compound of the present invention can also be suitably used as, forexample, a viscosity reducer.

The compound of the present invention can also be suitably used as, forexample, a dispersant, in particular, an aqueous dispersant.

The compound of the present invention can also be suitably used as, forexample, an emulsifier.

Surfactant

The present invention also provides a surfactant containing the compoundof the present invention described above. The compound of the presentinvention can be an active ingredient of the surfactant.

An aspect of the present invention can be a method for activating aninterface, comprising using the compound of the present invention.

The surfactant of the present invention may contain a substance(s) otherthan the compound of the present invention. Examples of such substancesinclude hydrocarbon-based surfactants.

Examples of hydrocarbon-based surfactants include compounds of formula:R—Y-M (wherein R is C₆₋₁₇ alkyl, Y is —ArSO₃—, —SO₃—, —SO₄—, —PO₃—, or—COO—, Ar is aryl, and M is H⁺, Na⁺, K⁺, or NH₄ ⁺).

Specific examples of hydrocarbon-based surfactants include sodiumdodecyl sulfate.

Such hydrocarbon-based surfactants are, for example, commerciallyavailable.

Hydrocarbon surfactants encompass anionic hydrocarbon surfactants,nonionic hydrocarbon surfactants, and cationic surfactants.

The following surfactants, including commercially available surfactants,are examples of hydrocarbon surfactants.

[1] Examples of anionic hydrocarbon surfactants include the following:(1) Versatic 10 (trade name, Resolution Performance Products), which isa highly branched C10 tertiary carboxylic acid;(2) Avanel S series (trade name, BASF), which are sodium linear alkylpolyether sulfonates;(3) Lankropol K8300 (trade name, Akzo Nobel Surface Chemistry), which isa sulfosuccinate surfactant;(4) (i) Emulsogen SB10 (trade name, Clariant) and (ii) Polirol (tradename) TR/LNA (trade name, Cesalpinia Chemicals), which are diisodecylsulfosuccinate, Na salt;(5) SilSense PE-100 Silicone (trade name, Noveon Consumer Specialties)and SilSense CA-A Silicone (trade name, Noveon Consumer Specialties),which are siloxane-based and anionic hydrocarbon surfactants; and(6) sodium dodecyl sulfate (SDS).[2] Examples of nonionic hydrocarbon surfactants, which are hydrocarbonsurfactants, include the following:(1) Triton X (trade name, Dow Chemical) series, which are octylphenolethoxylates;(2) Tergitol 15-S (trade name, Dow Chemical) series, which are branchedalcohol ethoxylates;(3) Dow Tergitol TMN (trade name, Dow Chemical) series, which arebranched secondary alcohol ethoxylates;(4) Tergitol L (trade name, Dow Chemical) series, which are ethyleneoxide/propylene oxide copolymers;(5) Pluronic R (trade name, BASF) series, which are difunctional blockcopolymers; and(6) TDA (trade name, BASF) series, which are tridecyl alcoholalkoxylates.[3] Examples of cationic surfactants, which are hydrocarbon surfactants,include cetyltrimethylammonium bromide (CTMAB).

The present invention also provides an aqueous dispersant containing thecompound of the present invention described above. The compound of thepresent invention can be an active ingredient of the aqueous dispersant.

An aspect of the present invention can be a method for dispersing anobject to be dispersed in an aqueous system, comprising using thecompound of the present invention.

EXAMPLES

Examples are given below to illustrate the present invention in moredetail; however, the present invention is not limited to these Examples.

The symbols and abbreviations in the Examples are defined as follows.

AIBN: azobisisobutyronitrile

Synthesis Examples Synthesis Example 1

Allyl bromide (1.7 eq.) and silver oxide (2.0 eq.) were added to adiethyl ether solution (100 mL) of diethyl tartrate (4.9 g), and themixture was stirred at 50° C. for 2 hours. Further, the mixture wasstirred at room temperature for 7 days. The reaction mixture wasfiltered, and the filtrate was concentrated to give compound 1 (6.3 g,92%).

A solution obtained by adding C₄F₉I (2.4 eq.) and AIBN (0.2 eq.) tocompound 1 (2.3 g) was heated at 80° C. for 18 hours. After thereaction, water was added, followed by extraction with chloroform. Thesolvent was distilled off from the extract to give compound 2 (6.0 g,76%).

Water and NMP were added to sodium hydrogen carbonate (2.0 eq.) andsodium hydrosulfite (2.0 eq.), and the mixture was stirred. Further,compound 2 (6.0 g) was added dropwise thereto, and the mixture wasstirred for 12 hours. Aqueous hydrochloric acid was added to thereaction mixture, followed by extraction with dichloromethane. Thesolvent was distilled off from the extract to give compound 3 (2.2 g,49%).

An aqueous sodium hydroxide solution (2.0 eq.) was added to a methanolsolution (10 mL) of compound 3 (2.2 g), and the mixture was stirred atroom temperature for 12 hours. Aqueous hydrochloric acid was added tothe reaction product solution, followed by extraction with ethylacetate. The solvent was distilled off from the extract to give compound4 (1.4 g, 71%).

An ammonia methanol solution (2.0 eq.) was added to a methanol solution(10 mL) of compound 4 (1.4 g), and the mixture was stirred at roomtemperature for 1 hour. After the reaction, the solvent was distilledoff to give compound 5 (1.5 g, quant.).

Synthesis Example 2

CF3COOCH3 (1.3 eq.) and triethylamine (2.0 eq.) were added to a methanolsolution (10 mL) of monoaminosuccinic acid (13 g), and the mixture wasstirred at room temperature for 17 hours. 1N aqueous hydrochloric acidwas added to the reaction mixture, and the mixture was extracted withethyl acetate. The solvent was distilled off from the extract, and thecrude product was recrystallized to give compound 8 (10 g, 44%).

An ammonia methanol solution (4.0 eq.) was added to a methanol solution(10 mL) of compound 8 (10 g), and the mixture was stirred at roomtemperature for 1 hour. Thereafter, the solvent was distilled off togive compound 9 (12 g, quant.).

Synthesis Example 3

In a manner similar to that of Synthesis Example 2, but using theconditions described in the above scheme, compound 6 (5.6 g, 26%) wassynthesized using monoaminosuccinic acid (6.5 g) as a starting material;subsequently, compound 7 (5.7 g, 95%) was obtained.

Synthesis Example 4

Trifluoroacetic anhydride (17 eq.) was added to a THF solution (5.0 mL)of diamine succinate (0.17 g), and the mixture was stirred for 24 hours.The reaction product solution was concentrated, dissolved in water, andextracted with ethyl acetate. The solvent was distilled off, and theobtained crude product was recrystallized to give compound 10 (0.13 g,29%).

A 3M ammonia methanol solution (4.0 eq.) was added to a methanolsolution (2.0 mL) of compound 10 (0.13 g), and the mixture was stirredat room temperature for 1 hour. Thereafter, the solvent was distilledoff to give compound 11 (0.08 g, quamt.).

Synthesis Example 4a

Perfluoropropionic anhydride (13.5 eq.) was added to a THF solution (7.5mL) of diamine succinate (0.37 g), and the mixture was stirred for 24hours. The reaction product solution was concentrated, dissolved inwater, and extracted with ethyl acetate. The solvent was distilled off,and the obtained crude product was recrystallized to give compound 15(0.21 g, 20%).

A 3M ammonia methanol solution (4.0 eq.) was added to a methanolsolution (2.0 mL) of compound 15 (0.05 g), and the mixture was stirredat room temperature for 1 hour. Thereafter, the solvent was distilledoff to give compound 16 (0.004 g, 73%).

Synthesis Example 5

Potassium carbonate (3.0 eq.) and H(CF₂CF₂)3CH2OH (3.0 eq.) were addedto a DMSO solution (5.0 mL) of 4,5-dichlorophthalonitrile (2.1 g), andthe mixture was stirred at room temperature for 11 days. Water was addedto the reaction product solution, followed by extraction withdichloromethane. The solvent was distilled off. Thereafter,recrystallization was performed to give compound 12 (0.7 g, 9.0%).

Sulfuric acid (9.0 mL) and water (3.0 ml) were added to compound 12, andthe mixture was stirred at 150° C. for 3 hours. After the reaction, 150mL of water was added to the reaction product solution, followed byfiltration. The crude product was recrystallized to give compound 13(0.42 g, 36%).

An ammonia methanol solution (4.0 eq.) was added to a methanol solution(10 mL) of compound 13, and the mixture was stirred at room temperaturefor 1 hour. Thereafter, the solvent was distilled off to give compound14 (0.21 g, 61%).

Measurement of Surface Tension

Measurement was performed using an ultrapure water solvent by theWilhelmy method (plate method), which is a classical method.

The table below shows the results.

TABLE 1 NH4 salt surface tension (mN/m) Compound 1 wt % 0.1 wt % 0.01 wt% Compound 7 38.4 44.8 50.7 Compound 9 48.9 49.7 50.2 Compound 11 36.244.8 49 Compound 16 30.2 37.8 40

1. A branched fluorine-containing compound represented by formula (1):(Rf—Y_(n1)LX-A)_(n2)  (1) wherein L represents (1) a trivalentcarbon-containing linker moiety represented by formula (L-1-1):

wherein R^(L), in each occurrence, is the same or different andrepresents hydrogen, alkyl optionally having at least one substituent,—NH₂, —NHR^(RL), —OH, or —OR^(RL), and R^(RL) represents an organicgroup, (2) a tetravalent carbon-containing linker moiety represented byformula (L-1-2):

wherein R^(L), in each occurrence, is the same or different andrepresents hydrogen, alkyl optionally having at least one substituent,—NH₂, —NHR^(RL), —OH, or —OR^(RL), and R^(RL) represents an organicgroup, (3) a pentavalent carbon-containing linker moiety represented byformula (L-1-2):

wherein R^(L) represents hydrogen, alkyl optionally having at least onesubstituent, —NH₂, —NHR^(RL), —OH, or —OR^(RL), and R^(RL) represents anorganic group, (4) a hexavalent carbon-containing linker moietyrepresented by formula (L-1-2):

(5) a tetravalent carbon-containing linker moiety represented by formula(L-2):

or (6) an (n1+n2)-valent carbon-containing linker moiety represented byformula (L-3):

wherein ring D represents an aromatic ring or a non-aromaticheterocycle; Rf, in each occurrence, is the same or different andrepresents fluoroalkyl optionally having at least one ether bond; Y, ineach occurrence, is the same or different and represents (1) a divalentlinking group selected from the group consisting of —O—, —COO—, —OCO—,—CONR^(Y)—, and —NR^(Y)CO— or (2) a bond, with the proviso that when Lis a trivalent carbon-containing linker moiety represented by formula(L-1-1) or a tetravalent carbon-containing linker moiety represented byformula (L-1-2), Y is not —COO— or —OCO—; R^(Y), in each occurrence, isthe same or different and represents hydrogen or an organic group; Lrepresents an (n1+n2)-valent carbon-containing linker moiety having atleast one carbon atom; n1 represents a number greater than or equal to1; n2 represents a number greater than or equal to 1; n1+n2 is a numberfrom 3 to 6; X, in each occurrence, is the same or different andrepresents a divalent linking group or a bond; A, in each occurrence, isthe same or different and represents —ArSO₃M, —SO₃M, —SO₄M, —PO₃M, or—COOM; M, in each occurrence, is the same or different and representshydrogen, —NR₄, or a metal salt; and R represents hydrogen or a C₁₋₄organic group.
 2. The branched fluorine-containing compound according toclaim 1, wherein L is a trivalent carbon-containing linker moietyrepresented by formula (L-1-1) or a tetravalent carbon-containing linkermoiety represented by formula (L-1-2); and Y, in each occurrence, is thesame or different and represents (1) a divalent linking group selectedfrom the group consisting of —O—, —CONR^(Y)—, and —NR^(Y)CO— or (2) abond.
 3. The branched fluorine-containing compound according to claim 2,wherein X is an alkylene chain or a bond.
 4. The branchedfluorine-containing compound according to claim 3, wherein X is a bond.5. The branched fluorine-containing compound according to claim 1,wherein L is a tetravalent carbon-containing linker moiety representedby formula (L-2); and at least one Y is —O—, —COO—, —OCO—, —CONR^(Y)—,or —NR^(Y)CO—.
 6. The branched fluorine-containing compound according toclaim 1, wherein n1 is 1 or 2; and n2 is
 2. 7. A surfactant comprisingthe branched fluorine-containing compound according to claim
 1. 8. Anaqueous dispersant comprising the branched fluorine-containing compoundaccording to claim 1.